Methyl 5-Bromolevulinate

Abstract

Methyl 5-bromolevulinate (30%) is obtained directly by brominating levulinic acid in methanol. The synthesis of 5-aminolevulinic acid over the 5-phthalimido ester thus becomes a three-step one.

Levulinic Acid Biorefineries: New Challenges for Efficient Utilization of Biomass

“…[129,130] The conventionalm echanism fort he production of DALA from LA involves the selective introductiono fa na mino group at the C5 position. The most common approach is the bromination of LA in an alcoholm edium to give mixtures of the 5-bromo-a nd 3-bromoesterst hat can be separated by distillation [131] and then 5-bromolevulinate is aminated by using nucleophilic nitrogen species. [132] The conventional synthesis of DALA is shown on Figure 5.…”

Production and catalytic transformation of levulinic acid: A platform for speciality chemicals and fuels

“…8. The most widely used approach for activating the C5 position in the amination process is the bromination of LA in an alcohol solvent to produce mixtures of 5-bromoesters and 3-bromoesters that are separated by distillation [102]. The 5-bromolevulinate is then aminated using a nucleophilic nitrogen species [103].…”

Synthesis of Bisubstrate Inhibitors of Porphobilinogen Synthase from Pseudomonas aeruginosa

“…TLC: silica gel 60 F 254 plates (aluminium, 0.2 mm; Merck). Flash column Methyl 5-Bromo-4-oxopentanoate (12) [24]. Br 2 (44 ml, 860 mmol) was added dropwise to levulinic acid (3; 100 g, 860 mmol) in MeOH (800 ml) at 08 for 2 h. After the addition was completed, the mixture was stirred at reflux for 90 min.…”

“…The bromo compound 12 was the precursor for the five targeted inhibitors 7 -11 and has already been described in the literature [24]. First, we tried to synthesize the Olinked diacid 7 using classical Williamson conditions (Scheme 2).…”